How to Manage Your Boss

It’s not easy being the boss. Your manager’s job is to provide direction. Yours is to get the work done – and done right. But management can be a two way street, and whether or not you’re seen as a valuable asset depends in part on how well you do these three things.

Ask questions. Never attend a project meeting without taking notes; don’t rely on your memory, especially in a dynamic discussion. Good questions show you’re listening, and help to clarify. “Will this be a similar project to the ABC Company merger last year?” “Would the report format I used for the Johnson case be appropriate?” Asking about precedents helps to clarify the scope of a new project.

Your questions should always include deadlines (see below) and resources. Ask about budgets and who you’ll be working with, and send a quick email to summarize the project after your meeting. Your manager can correct immediately any errors or assumptions you’ve made, saving you time and frustration later.

The most powerful question a worker can ask is “What if?” It signals that you’re thinking ahead and innovating. “What if we tried it from another angle?” can be a way to help your manager find creative solutions. Questions like “What if the client funding falls through?” show that you’re thinking ahead and preparing for contingencies. Be careful here: one or two “What ifs” are helpful to your boss; more than a few may peg you as fearful of taking risks or obstructive.

Give progress reports. When your manager delegates a task or a project, you should always try to get a sense of how urgent it is. Even the simplest of tasks may become burning issues when they impact others. “Would you please make a copy of these reports?” is a very different request than “Please make copies of these – the CFO is waiting for them upstairs.” If you don’t get a sense of how critical a task is, ask. If your boss doesn’t give you a deadline for a project, ask for one. It’s crucial that you understand which projects take priority over others.

It never hurts to let your boss know when you’ve finished something. A quick email to say “I connected with Mr. Jones, and we have an appointment on Tuesday” closes the loop and helps your boss cross another item off her “to-do” list. Likewise, when you’re having trouble finishing a project, inform her. Notes or emails that say “I just wanted to let you know – I haven’t been able to get the data yet, but it should be available early next week” notify your manager that you’re still working on the project, and haven’t forgotten about it or let it languish.

Knowing how to manage deadlines is another important skill. Don’t delay telling your manager that you’re going to miss a deadline – tell him as early as you can. You should know from experience how much time your manager builds into a deadline. If he’s a last minute person, he’s going to have less flexibility in his timeline. If he’s a structured planner, he’ll have more flexibility, but be more distressed by delays. Either way, he’ll want to know as early as possible that the deadline will have to be changed.

Deliver bad news. Everyone has had to deliver bad news at some point. It’s never easy, but you can minimize the damage. First, try to have all the facts, including the worst of the news, before you go in. A good manager will want to know the worst case scenario. You should have it ready. If you can, offer possible solutions with the news – after all, you’ve had time to think about it longer than your boss. What managers do best is make decisions, so her natural instinct will be to ask for alternatives to act on. Whatever the situation, it’s never a good idea to come in blaming others; if you’re delivering the news, you must have had a stake in what happened. Be forthright about the role you played in the disaster, and focus on how to fix it. Bad things happen in every career; it’s how you handle them that determines how bright your future will be.

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